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Chemical Compound Review:

AC1NUSGS (2R,3R)-2,3-dihydroxy-4- phosphonatooxy...

Synonyms: CHEBI:16897, 585-18-2, 4-O-phosphonato-D-erythrose, (2R,3R)-2,3-dihydroxy-4-oxobutyl phosphate, [(2R,3R)-2,3-dihydroxy-4-oxobutyl] phosphate

This record was replaced with 122357.

Sundaram, A.K. et al., Wu, J. et al., Shumilin, I.A. et al., Ohashi, K. et al., Schoner, R. et al., et al.

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Disease relevance of ERYTHOSE-4-PHOSPHATE

The tyrosine-sensitive 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (7-phospho-2-keto-3-deoxy-D-arabino-heptonate D-erythrose-4-phosphate lyase (pyruvate-phosphorylating), EC 4.2.1.15) was purified to homogeneity from extracts of Escherichia coli K12 [1].
[figure: see text] Neisseria gonorrhoeae 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAH 7-P) synthase catalyzes an aldol-type condensation between D-erythrose 4-phosphate and phosphoenolpyruvate (PEP) to form 3-deoxy-D-arabino-heptulosonate 7-phosphate and not 3-deoxy-D-riboheptulosonate 7-phosphate [2].

High impact information on ERYTHOSE-4-PHOSPHATE

Based on the precedent of the d-erythrose-4-phosphate (E4P) modeled in the active site of DAHPS, we have modeled PEP and A5P in KDOPS and compared the coordination of PEP and A5P in KDOPS with that of PEP and E4P in DAHPS [3].
By gas chromatography/mass spectrometry, we observed that D-threose 4-phosphate was also converted into D-erythrulose 4-phosphate and D-erythrose 4-phosphate [4].
Purification and properties of beef liver aldehyde reductase catalyzing the reduction of D-erythrose 4-phosphate [5].
The enzyme displays a homotetrameric structure in solution and appears to follow Michaelis-Menten kinetics with K(m)(PEP)=139+/-11.4 microM for phosphoenolpyruvate, K(m)(E4P)=1760+/-110 microM for D-erythrose 4-phosphate, kcat=4.6+/-0.1 s(-1) for DAHPS activity and K(m)(chorismate)=850+/-97 microM, kcat=0.41+/-0.01 s(-1) for CM activity [6].

Associations of ERYTHOSE-4-PHOSPHATE with other chemical compounds

3-Deoxy-D-arabino-heptulosonate-7-phosphate synthase (DAHPS), the first enzyme of the aromatic biosynthetic pathway in microorganisms and plants, catalyzes the aldol-like condensation of phosphoenolpyruvate and D-erythrose-4-phosphate with the formation of 3-deoxy-D-arabino-heptulosonate-7-phosphate [7].

Analytical, diagnostic and therapeutic context of ERYTHOSE-4-PHOSPHATE

Enzymatic isomerization and epimerization of D-erythrose 4-phosphate and its quantitative analysis by gas chromatography/mass spectrometry [4].

References

3-Deoxy-D-arabino-heptulosonate 7-phosphate synthase. Purification, properties, and kinetics of the tyrosine-sensitive isoenzyme from Escherichia coli. Schoner, R., Herrmann, K.M. J. Biol. Chem. (1976) [Pubmed]
Neisseria gonorrhoeae 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase does not catalyze the formation of the ribo analogue. Sundaram, A.K., Woodard, R.W. Org. Lett. (2001) [Pubmed]
3-Deoxy-D-manno-octulosonate-8-phosphate synthase from Escherichia coli. Model of binding of phosphoenolpyruvate and D-arabinose-5-phosphate. Wagner, T., Kretsinger, R.H., Bauerle, R., Tolbert, W.D. J. Mol. Biol. (2000) [Pubmed]
Enzymatic isomerization and epimerization of D-erythrose 4-phosphate and its quantitative analysis by gas chromatography/mass spectrometry. Ohashi, K., Terada, T., Kohno, T., Hosomi, S., Mizoguchi, T., Uehara, K. Eur. J. Biochem. (1984) [Pubmed]
Purification and properties of beef liver aldehyde reductase catalyzing the reduction of D-erythrose 4-phosphate. Terada, T., Kohno, T., Samejima, T., Hosomi, S., Mizoguchi, T., Uehara, K. J. Biochem. (1985) [Pubmed]
Bacillus subtilis 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase revisited: resolution of two long-standing enigmas. Wu, J., Sheflyan, G.Y., Woodard, R.W. Biochem. J. (2005) [Pubmed]
Allosteric inhibition of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase alters the coordination of both substrates. Shumilin, I.A., Zhao, C., Bauerle, R., Kretsinger, R.H. J. Mol. Biol. (2002) [Pubmed]

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